Trifluoroacetic acid → HCID 86585660, compound

HRID 1358917Notes

Reaction equation

HRID 1358917 reaction equation
C([O:5][C:6]([C:8]1[N:9]2[CH:12]([S:13][CH2:14][C:15]=1[S:16][C:17]1[S:18][C:19]([NH2:22])=[N:20][N:21]=1)[C@H:11]([NH:23][C:24](=[O:57])[C:25]([C:31]1[N:32]=[C:33]([NH:37]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[S:34][C:35]=1[Cl:36])=[N:26][O:27][CH2:28][CH2:29][F:30])[C:10]2=[O:58])=[O:7])(C)(C)C.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[NH2:37][C:33]1[S:34][C:35]([Cl:36])=[C:31]([C:25](=[N:26][O:27][CH2:28][CH2:29][F:30])[C:24]([NH:23][C@@H:11]2[C:10](=[O:58])[N:9]3[CH:12]2[S:13][CH2:14][C:15]([S:16][C:17]2[S:18][C:19]([NH2:22])=[N:20][N:21]=2)=[C:8]3[C:6]([OH:7])=[O:5])=[O:57])[N:32]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 86585658HCID 86585658, compound

Product 1

HCID 86585660HCID 86585660, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (7R)-7-[2-[5-chloro-2-(tritylamino)-thiazol-4-yl]-2-(2-fluoro-ethoxyimino)-acetylamino]-3-(5-amino-[1,3,4]thiadiazol-2-ylsulfanyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid t-butyl ester (8 mg, 0.009 mmol) in dichloromethane (0.16 mL) was added triethylsilane (0.04 mL), followed by trifluoroacetic acid (0.16 mL). After 3 hr at room temperature the reaction mixture was concentrated under vacuum and disopropyl ether was added to the oily residue. The title compound precipitated and was filtered, washed with additional diisopropyl ether and dried under vacuum (3 mg, 32%).

Workup

  1. concentrationAfter 3 hr at room temperature the reaction mixture was concentrated under vacuum and disopropyl ether
  2. additionwas added to the oily residue
  3. customThe title compound precipitated
  4. filtrationwas filtered
  5. washwashed with additional diisopropyl ether
  6. customdried under vacuum (3 mg, 32%)

Sources & evidence

ORD record
ord-df66feea0c5a43c198b10e36c8cc3226
Source dataset
uspto-grants-2003_07
Patent number
US06599893B2

Reaction notes

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